The Innovation Stack: How Square Co-Founder Jim McKelvey Thinks About Disruption

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“Know what side of the line of innovation you’re on.”


When Jim McKelvey and Jack Dorsey were building Square, they were met with legal issues, major challenges from Amazon, and more. But necessity is the mother of innovation, and anger is the fuel that kept Jim going. Hear the lessons Jim and Jack learned and where Jim thinks the world of content is headed on this episode.

Key Insights


How do you beat Amazon? (2:00)

There is no fool-proof answer to that question, but Jim explains that there are things brands should consider when thinking about how to compete against the Amazons of the world. And what is the biggest indicator of success against Amazon? Innovation.

“Do you have a truly new product? Something that has, what I call, an innovation stack, something that has multiple ways of differentiating itself. If that’s the case, you can pretty much ignore Amazon. And I know that’s crazy. If they copy you, it doesn’t matter. If you are derivative, in other words, if you’re doing something that has been done before and there are trade shows on your topic and there are experts and their consultants and it’s a known ecosystem, you’re probably dead.”

Is your time actually yours? (15:00)

We all want to take control of our time and waste as little of it as possible. But that is getting harder and harder. In order to take control back, we have to put technology to use in new, innovative ways, which Jim is building at Invisibly.

“I think we’re all pretty good stewards of our own time if we are given the chance to be. The problem is that so much of our queue is not created by us. It’s created by others. So, my inbox is like this to-do list… If you send me this email, you just gave me a to-do. Now, maybe the only thing I have to do is delete it because I don’t recognize you. But then there’s that weird email from my doctor, or some friend, or somebody who I actually like who gets in, I actually have to spend a little time looking. So, even your stupid email that I will delete and never read, I have to pay some attention to. And that drains me. And then, take the world of social media or the feeds that we’re so subjected to. And it’s 10 times worse because then, what’s happening is your attention is being routed to subjects that are for the benefit of the platform.”

Can you incentivize good content and, as a result, save journalism? (26:00)

Media companies have a problem with making money and consumers have a problem with finding content that helps them. The solution is coming up with a way to incentivize the creation of good content.

“The question is how do we bring back the incentive to edit, to create quality, to distill quality? Because I’m not going to run out of anything except time. That’s what that 90-year calendar is. That’s basically a reminder that the first thing that we all run out of humans is not money, it’s time. So, how do I make better use of my time? And the answer is I consume things more efficiently, but I can’t do that by myself. The producer has to do that. And the producer’s only going to do that if they’re paid to do that.”

About the Guest:

“Jim McKelvey co-founded Square, where he now serves as a Director. Jim is also a General Partner at FINTOP Capital and Green Visor Capital. He serves as a Director of the St. Louis Federal Reserve and as a Trustee to Washington University in St. Louis.

Jim’s first venture was co-founding Mira Digital Publishing in 1990, which is a leader in electronicpublishing for scientific conferences. In 2013, he founded the LaunchCode Foundation, currently bringing free computer education and jobs to 5 US cities. In addition to his businesses and philanthropy, Jim is a glassblowing artist and co-founded one of the nation’s top glass centers, Third Degree Glass Factory. He has published two books on computer programming and one on glassblowing. He is a graduate of Washington University in St. Louis.”


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Episode 198